What Happened To Alexis Bledel And Milo Ventimiglia's Relationship
He was the boy who wasn't supposed to happen to Rory Gilmore's picture-perfect existence! When Jess Mariano arrived in Stars Hollow during Gilmore Girls' second season, Rory Gilmore's life couldn't have been going better; She was just accepted to the prestigious Chilton Academy, bringing her one step closer to achieving her dream of attending Harvard for college, she had her best friend Lane to help her through those tough times spent in Chilton's hallowed halls with stubborn academically-minded popular girls and of course, the endless caffeine-fueled romps with her mother Lorelai. To top it off, she had everyone's favorite floppy-haired grocery guy Dean for the perfect first boyfriend. Nothing could go wrong, right?
Before Rory knew it, there was a new guy in town, a tall and mysterious fella who quickly earned the title of Stars Hollow's bad boy. The mysterious Jess was quickly intriguing; he loved to read, he spoke in rapid-fire pop culture references just like her, and to make matters even tougher, he was Luke Danes' nephew; Since Luke served as Lorelai and Rory's lifeline to their precious coffee, there would be no avoiding Jess!
Rory and Jess' chemistry and interest in one another was palpable nearly from the beginning. As it turns out, the chemistry and intrigue leaped off the pages of the Gilmore Girls' scripts and into the real-life hearts of the pair who brought the couple to life; Alexis Bledel and Milo Ventimiglia were quite smitten with one another, and they began dating off-camera as well: A match made in 'Literati' heaven!
An Inside Look Into Alexis And Milo's Real-Life Romance
Rory and Jess shared lots of things; The pair's banter could make even the shiest person swoon, they had cute nicknames for each other, (remember when Rory called him 'Dodger' after he swiped one of her books, and he jokingly called her Courtney Love to his Kurt Cobain before he crashed Rory's first car?) and racked up many memorable kisses during their relationship.
There was plenty of lip-locking to be had between the pair behind-the-scenes! Bledel and Ventimiglia caught one another's attention after Ventimiglia joined the cast, and the pair began dating in 2002 just as Rory and Jess' romance was heating up on-screen. Understandably, there was lots of hope from fans to see real-life moments between the couple akin to Rory and Jess' cutest moments, but aside from the occasional photograph together at an event, there wasn't much for the public to sink their teeth into to satisfy their craving for hot Alexis and Milo related gossip.
How Serious Were The Pair?
The debate over the perfect boyfriend for Rory Gilmore was a hot-button issue for Gilmore devotees throughout the series' seven-season run. Jess and Rory called it quits for good after Jess couldn't commit, and he briefly popped up in Rory's life again in the sixth season to give her a little nudge after she briefly split up with her arguable truest love, academia. Jess even returned briefly in the series' Netflix revival from 2016, where he again helped his golden Gilmore Girl through a bind; there was even a split second moment where the audience catches Jess longingly gazing at Rory through a window, implying he was thinking about what could've been between the pair.
The idea of 'What could've been' applies to Bledel and Ventimiglia's real-life relationship, too! Despite her normally tight-lipped nature about their relationship, Bledel once dropped the 'M' word in an interview with People magazine back in 2005, elaborating that the duo had "Talked about" taking the big step to tie the knot, before implying the couple wasn't in a hurry to get married.
From 'Serious' To A 'Sudden Split'
Unfortunately, like both Rory and her mother, Alexis Bledel didn't make it down the aisle with her 'Gilmore guy.'
As things with Rory and Jess seemed to look promising for a brief moment in 2006 when Ventimiglia came back for a guest appearance, Bledel and Ventimiglia's relationship was cooling down off-screen. The pair officially split up in 2006. The pair never gave a public explanation for their split, but the duo always remained cordial when talking about one another in the press. Their relationship had been repaired and hearts and any potential hard feelings had dissipated by the time the two reunited on-screen to film A Year In The Life. Ventimiglia even gave Bledel a shout-out a year later after the duo had both experienced respective successes on their post-Gilmore television shows, and Bledel received critical acclaim for her work on The Handmaid's Tale.
These days, Bledel's heart is taken by another television hunk- Vincent Kartheiser, whom she met on the set of Mad Men. Kartheiser and Bledel got married in 2014 and secretly welcomed a child soon afterward. Ventimiglia's matters of the heart have been kept a bit more private, but fans have been able to watch him heat up the small screen with Bledel's one-time Vanity Fair cover mate, Mandy Moore, in the critically acclaimed TV series This Is Us, which is currently in its fifth season.
Luckily for those who have never gotten over Bledel and Ventimiglia's real-life break-up, their on-screen romance lives on through caffeine-fueled marathons of Gilmore Girls on Netflix to soothe any sadness!
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